GB1008645A - Dibenzocycloheptane derivatives - Google Patents

Dibenzocycloheptane derivatives

Info

Publication number
GB1008645A
GB1008645A GB31052/63A GB3105263A GB1008645A GB 1008645 A GB1008645 A GB 1008645A GB 31052/63 A GB31052/63 A GB 31052/63A GB 3105263 A GB3105263 A GB 3105263A GB 1008645 A GB1008645 A GB 1008645A
Authority
GB
United Kingdom
Prior art keywords
prepared
alkyl
cycloheptadien
dibenzo
yloxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB31052/63A
Inventor
Gerardus Johannes Bertra Corts
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Koninklijke Pharmaceutische Fabrieken NV
Original Assignee
Koninklijke Pharmaceutische Fabrieken NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Priority to GB31052/63A priority Critical patent/GB1008645A/en
Priority to US344235A priority patent/US3396168A/en
Priority to NL6401261A priority patent/NL6401261A/xx
Priority to DK9165AA priority patent/DK105650C/en
Priority to SE1810/64A priority patent/SE318889B/xx
Priority to CH176464A priority patent/CH450431A/en
Priority to BE643796D priority patent/BE643796A/xx
Priority to NO152015A priority patent/NO115337B/no
Priority to DK72764AA priority patent/DK104352C/en
Priority to DE19641470131 priority patent/DE1470131A1/en
Priority to FR963927A priority patent/FR4185M/fr
Publication of GB1008645A publication Critical patent/GB1008645A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Vehicle Body Suspensions (AREA)

Abstract

The invention comprises N-substituted-3-(dibenzo[a,d] - 1,4 - cycloheptadien - 5 - yloxy) nortropane derivatives of formula <FORM:1008645/C2/1> where R1 and R2 represent hydrogen, halogen or C1- 4 alkyl, R3 represents C2- 8 alkyl or aralkyl with up to 8 carbon atoms in the alkyl moity, and their non-toxic acid addition salts. They are prepared by: (1) reacting <FORM:1008645/C2/2> with <FORM:1008645/C2/3> preferably in the presence of an acid-binding agent or using an alkali metal salt of the nortropine; (2) reacting a compound of formula <FORM:1008645/C2/4> with R3 Hal or with R31 CO Hal (R31=C1- 7 the alkyl moity) followed by reduction of the carbonyl group, e.g. with LiAlH4; or (3) reacting a compound of formula <FORM:1008645/C2/5> with R31CHO under reducing conditions (R4 H or COOH). N-Ethylnortropine is prepared H2/Raney nickel reduction of N-ethylnortropinone. 3 - (Dibenzo[a,d] - 1,4 - cycloheptadien - 5 - yloxy) - 8 - octanoylnortropane is prepared from 3-(dibenzo[a,d]-1,4-cycloheptadien-5-yloxy) nortropane and octanoyl chloride. N - (b - Phenylethyl) nortropine is prepared from N-carboxynortropine and phenylacetaldehyde in the presence of hydrogen and Raney nickel. The compounds of the invention possess spasmolytic, antihistaminic and local anaesthetic activity. Inorganic and organic salts are specified. They may be administered orally as tablets, pills or capsules or parenterally. Specifications 943,603 and 988,291 are referred to.
GB31052/63A 1963-08-06 1963-08-06 Dibenzocycloheptane derivatives Expired GB1008645A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB31052/63A GB1008645A (en) 1963-08-06 1963-08-06 Dibenzocycloheptane derivatives
US344235A US3396168A (en) 1963-08-06 1964-02-12 Dibenzocycloheptane derivatives
NL6401261A NL6401261A (en) 1963-08-06 1964-02-13
DK9165AA DK105650C (en) 1963-08-06 1964-02-14 Process for the preparation of N-substituted 3- (dibenzo (a, d) -1,4-cycloheptadien-5-yloxy) -nortropane derivatives or their acid addition salts.
SE1810/64A SE318889B (en) 1963-08-06 1964-02-14
CH176464A CH450431A (en) 1963-08-06 1964-02-14 Process for the preparation of new nitrogen-substituted 3- (dibenzo (a, d) -1,4-cycloheptadien-5-yloxy) -nortropanes
BE643796D BE643796A (en) 1963-08-06 1964-02-14
NO152015A NO115337B (en) 1963-08-06 1964-02-14
DK72764AA DK104352C (en) 1963-08-06 1964-02-14 Process for the preparation of N-substituted 3- (dibenzo (a, d) -1,4-cycloheptadien-5-yloxy) -nortropane derivatives or their acid addition salts.
DE19641470131 DE1470131A1 (en) 1963-08-06 1964-02-15 Process for the preparation of new nitrogen-substituted 3- (dibenzo [a, d] -1,4-cycloheptadien-5-yloxy) nortropanes, salts of these compounds, and pharmaceutical preparations which contain these compounds or their non-toxic salts
FR963927A FR4185M (en) 1963-08-06 1964-02-15

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31052/63A GB1008645A (en) 1963-08-06 1963-08-06 Dibenzocycloheptane derivatives

Publications (1)

Publication Number Publication Date
GB1008645A true GB1008645A (en) 1965-11-03

Family

ID=10317249

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31052/63A Expired GB1008645A (en) 1963-08-06 1963-08-06 Dibenzocycloheptane derivatives

Country Status (10)

Country Link
US (1) US3396168A (en)
BE (1) BE643796A (en)
CH (1) CH450431A (en)
DE (1) DE1470131A1 (en)
DK (2) DK105650C (en)
FR (1) FR4185M (en)
GB (1) GB1008645A (en)
NL (1) NL6401261A (en)
NO (1) NO115337B (en)
SE (1) SE318889B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7888358B2 (en) 2003-06-24 2011-02-15 Neurosearch A/S 8-aza-bicyclo[3.2.1]octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1142610A (en) * 1966-12-12 1969-02-12 Koninklijke Pharma Fab Nv Ketoxime ethers
US3536719A (en) * 1967-01-25 1970-10-27 Koninklijke Pharma Fab Nv Tropinyl and quinuclidinyl ethers of certain azadibenzocyclohepten-5-ols and derivatives thereof
US3513788A (en) * 1968-10-08 1970-05-26 Albert Ostrin Rotary incinerator with spinning cup burner
AU5088993A (en) * 1992-08-24 1994-03-15 President And Fellows Of Harvard College Cocaine analogues and their use as cocaine drug therapies and therapeutic and imaging agents for neurodegenerative disorders
EP1838705A2 (en) * 2005-01-13 2007-10-03 Neurosearch A/S 3,8-substituted 8-aza-bicyclo [3.2.1] octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3119829A (en) * 1959-04-01 1964-01-28 Koninklijke Pharma Fab Nv 5-tropinyl dibenzocycloheptene derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7888358B2 (en) 2003-06-24 2011-02-15 Neurosearch A/S 8-aza-bicyclo[3.2.1]octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors

Also Published As

Publication number Publication date
DK104352C (en) 1966-05-09
US3396168A (en) 1968-08-06
DE1470131A1 (en) 1969-04-24
CH450431A (en) 1968-01-31
NO115337B (en) 1968-09-23
BE643796A (en) 1964-08-14
NL6401261A (en) 1965-02-08
FR4185M (en) 1966-05-31
SE318889B (en) 1969-12-22
DK105650C (en) 1966-10-24

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